2-Methoxy-5-nitroaniline → HCID 307331, compound

HRID 2392669Notes

Reaction equation

HRID 2392669 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:20]1([CH2:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH:5][C:27](=[O:28])[CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 74472-Methoxy-5-nitroanilineHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 10340Sodium Carbonate

Product 1

HCID 307331HCID 307331, compoundYield 108.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-methoxy-5-nitroaniline (4.86 g, 0.029 mole) and triethylamine (5.2 ml, 0.037 mole) in dichloromethane (150 ml) at 0° C. was treated with phenylacetyl chloride (5.0 ml, 0.037 mole). The mixture was stirred for 0.5 h, then treated with water (20 ml), stirred for a further 20 mins., then basified with Na2CO3 and extracted with dichloromethane. The extract was washed with dil. HCl acid/brine, then dried (Na2SO4) and concentrated in vacuo to afford the title compound as a brown solid (9.0 g, 100%).

Workup

  1. stirringstirred for a further 20 mins
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with dil. HCl acid/brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fecef7372564ea88c6908c00f5fac07
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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